Imparting deodorizing and antibacterial effects to the hair with bifunctional antioxidants

ABSTRACT

Cosmetic compositions for hair containing a compound of the formula (1)   WHEREIN N IS 0 OR 1, R1 is an aliphatic hydrocarbon radical having 8 to 14 carbon atoms or a tertiary butyl radical and R2 and R3 each are hydrogen or alkyl or hydroxyalkyl having 1 or 2 carbon atoms, with the proviso that at least one of R2 and R3 is said alkyl or hydroxyalkyl.

United States Patent [191 Arai et a1.

[451 Sept. 2, 1975 i 1 IMPARTING DEODORIZING AND ANTIBACTERIAL EFFECTSTO THE HAIR WITH BIFUNCTIONAL ANTIOXIDANTS [75] Inventors: HaruhlkoArai, Narashino; .Iunryo Mlno, Kamagaya; Shigeo lnoue, Tokyo, all ofJapan [73] Assignee: Kao Soap Co., Ltd., Tokyo, Japan [22] Filed: Sept.24, 1973 [21 Appl. No.: 400,257

[30] Foreign Application Priority Data Sept. 26. 1972 Japan 47-96448[52] US. Cl. 424/65; 252/106; 252/107; 424/D1G. 4; 424/70; 424/337;424/365 [51] Int. Cl. A61K 7/32; A01N 9/12; A61K 7/06 [58] Field ofSearch 424/DIG. 4, 337, 65, 70; 260/609 R; 252/106, 107

Primary Examt'n0rAlbert T. Meyers Aas'istant Examiner-Vera C. ClarkeAttorney, Agent, or Firm-Woodhams, Blanchard and Flynn 5 7 ABSTRACTCosmetic compositions for hair containing a compound of the formula 1(c11 s (ca on m wherein n is 0 or 1, R is an aliphatic hydrocarbonradical having 8 to 14 carbon atoms or a tertiary butyl radical and Rand R each are hydrogen or alkyl or hydroxyalkyl having 1 or 2 carbonatoms, with the proviso that at least one of R and R is said alkyl orhydroxyalky].

2 Claims, No Drawings IMPARTING DEODORIZING AND ANTIBACTERIAL EFFECTS TOTHE HAIR WITH BIFUNCTIONAL ANTIOXIDANTS BACKGROUND OF THE INVENTIONFIELD OF THE INVENTION This invention relates to cosmetic compositionsfor hair, more specifically, shampoos, hair-rinsing agents, hairlotions, hair oils, hair creams and pomades, which compositions canimpart durable antibacterial and deodorizing effects to the surface ofhair.

Table l Bactcriostatic Action of 4 4'Thiohis (6Tcrt.But)lIMMethylphcnol) Gram Positive Bacteria Gram Negative Bacte riaStaphylococcus Bacillus Escherichia aureus suhtilis coli 4,4- thiohis(6-tert. Concentration Concen trution Concentration hutyl3-methylphenol) 5()()ppm 5(lppm 5(l0ppm Slippm SUUppm 5(lppm According tothe agar streak test method; v means the inhibition ol'grouth oftheIIHCIL'I'IAI',

means no inhibition of growth of bacteria SUMMARY OF THE INVENTION Wehave discovered that compounds of the formula no (cn -s- (cn i 0H (1)wherein n is O or 1, R is an aliphatic hydrocarbon radical having 8 to14 carbon atoms, especially alkyl of 8 to 14 carbon atoms, or a tertiarybutyl radical, and R and R each are hydrogen or alkyl having 1 to 2carbon atoms or hydroxyalkyl having 1 to 2 carbon atoms, with theproviso that at least one of R and R is said alkyl or hydroxyalkylgroup, have the following advantageous effects:

1. excellent bacteriostatic action against Gram positive bacteria whichare included in the class of saprogenous bacteria;

2. preventing rancidity caused by autoxidation of sebum componentssecreted from the skin of human heads;

3. they are effectively deposited and adhered on the skin of human headsby various hair treatment operations such as washing, rinsing andapplication of hair grooming aids.

This invention provides cosmetic compositions for hair containing acompound or mixture of compounds of the formula (1). The compositions ofthe invention possess dandruff alleviating and deodorizing properties.

Because of the presence of the long chain alkyl group and the benzenering, the compounds further possess an excellent adherence to hair andthe skin of human heads.

The desired effects of this invention can be attained by applying andadhering compounds of the formula (1) on the skin and hair of humanheads. For this purpose, the following three typical methods ofapplication can be used:

1. A compound of the general formula l is incorporated in an amount ofabout 0.001 to about 2 percent by weight into a shampoo composition forremoving dirt, fat and loose corneal cells from the skin and hair ofhuman heads, which shampoo composition comprises as a principaleffective ingredient an anionic sur face active agent.

2. A compound of the general formula l is incorpo rated in an amount ofabout 0.001 to about 2 percent by weight into a hair rinsing compositionfor improving the softness, lustre and manageability of hair, which hairrinsing composition comprises as a principal effective ingredient acationic surface active agent.

3. A compound of the general formula l is incorporated in an amount ofabout 0.00l to about 2 percent by weight into a hairgrooming aid usedfor applying various materials, such as emollients, perfumes, etc., tothe skin and hair of human heads and adjusting hair styles, such aspomades, hair creams, hair oils or hair lotions, which hairgroomingcomprises as a substrate an oily, alcoholic or aqueous substance.

Compounds of the formula (1) can be incorporated in conventionalcosmetic compositions for hair including shampoos, rinses andhairgrooming aids. Rinses containing temporary colorants, such aswater-soluble dyes can be used. However, the invention does notcontemplate the use of the compounds of formula (1) in hair treatingcompositions which impart a lasting effect, such as permanent hair dyesand bleaches.

Hair shampoos that can be used include clear liquid shampoos, creamshampoos, gel shampoos and the like. Such shampoos are aqueous solutionsusually containing from about to about 30 weight percent of detergent.The detergent can be selected from those conventionally used for thispurpose including soaps such as potassium soaps of coconut oil and othervegetable oils, fatty alcohol sulfates such as sodium dodecyl sulfateand various other anionic detergents. The shampoo compositions cancontain various adjuncts such as calcium salt dispersing agents,sequestrants, solvents, thickening agents, hair and skin conditioningagents, finishing agents, foam builders, perfumes and preservatives.

Hair rinses that can be used are aqueous solutions of cationicdetergents, such as alkyl (C -C dimethylbenzyl ammonium chlorides,usually employed in low concentrations of about 1 to 3 weight percent.The hair rinses can contain various hair conditioning agents,thiekeners, solvents, perfumes, watersoluble dyes, etc.

The hairgrooming aids that can be used include brilliantines, pomades,hair oils, hair creams (water-in-oil, oil-inwater or dual emulsiontype), alcohol-based hair lotions and two-phase hair lotions.Brilliantine is comprise mainly of mineral oil and waxes. Pomades arecomprised mainly of animal and vegetable fats. Hair oil isco'rhprisedmainly of mineral oil and can contain vegetable oils. The brilliantine,pomade and hair oil compositions are anhydrous. They normally containperfume. Hair creams are emulsions of water and oil. W/O emulsionsgenerally contain 30 to 60 weight percent water, 30 to 50 weight percentoils, plus emulsifying agents, perfumes, etc. Dual emulsions aresimilar, but employ beeswax/borax or nonionic emulsifiers. O/W emulsionsgenerally contain 60 to 90 weight percent water, 10 to 30 weight percentoil materials and the balance is various adjuncts. Alcohol-based hairlotions consist primarily of a solution of water-soluble alcohols suchas ethanol or isopropyl alcohol, water and perfume oil. Two phase hairlotions consist primarily of an aqueous solution of water-solublealcohol as one phase, mixed with an oil as the second phase.

The hair shampoos, hair rinses and hairgrooming aids, which serve as abase or carrier for the compounds of formula 1) according to thisinvention, can be of any suitable conventional formulation compatiblewith the compounds of formula (1). Suitable formulations of specificcompositions will be readily apparent to workers in the cosmetic art.Since the present invention can employ the conventional shampoos, rinsesand hairgrooming aids, it is believed unnecessary to describe same ingreater detail herein.

The cosmetic compositions for treating hair containing one or morecompounds of formula l according to the invention, can be applied tohair in accordance with the conventional techniques. The compound offormula (1) will remain adhered to the hair and scalp in an amounteffective to alleviate dandruff and to reduce odor.

This invention will now be further described by reference to thefollowing Examples.

EXAMPLE 1 A shampoo'composition was prepared according to the followingrecipe:

Panel tests were conducted comparing the use of the above compositionaccording to this invention and, as a control, the same composition freeof 4,4'-thiobis( 6- tert.-butyl-2-methylphenol). More specifically, eachof the above two compositions were applied for one month, respectively,to panels of test subjects each consisting of 10 men normally troubledwith excessive dandruff. At the end of the test period, the scalps ofthe test subjects were examined. In the case of the composition of thisinvention, in 8 men no loose dandruff was observed and no crusts werepresent on the head skin. In the remaining 2 men no scab-like wetdandruff such as is seen in the case of an ordinary commercial shampoowas observed, and the head skin was clean. In the case of the controlshampoo free of the active ingredient of this invention, the head skinof the test subjects showed dandruff after the treatment, the same as inthe case of an ordinary commercial shampoo. Thus, it was shown that thecomposition of this invention has an excellent dandruff-alleviatingeffect.

EXAMPLE 2 A hair rinsing composition was prepared according to thefollowing recipe:

Hair treated with the above rinsing composition had a beautifulappearance, and the composition exhibited excellent dandruff-alleviatingand deodorizing effects.

EXAMPLE 3 A hairgrooming aid composition was prepared according to thefollowing recipe:

Components percent by weight Fluid paraffin 16.0 Hydrous lanolin 7.0 Wax2.0 Trioxyethylene lauryl ether 40 Polyoxyethylene( l 0 )monostearate20.0

-Continued Components percent by weight Bis(Z-methyl-4-hydroxy-5-octylhenzyl) 0.2

thioether Perfume 0.5 Water bulunce This composition exhibited excellenthair styling, del (CH -s- (CH wherein n is zero or one, R, is octyl ortertiary butyl,

0 and R and R each is hydrogen or alkyl having one or 2 carbon atoms,provided that at least one of R and R is said alkyl.

2. The method according to claim 1, in which a hair shampoo, a hairrinse or a hairgrooming aid containing from about 0.001 to about 2.0percent by weight of said compound is applied.

i it l i '3'

1. A METHOD FOR IMPARTING A DURABLE ANTIBACTERIAL AND DEODORIZING EFFECTTO THE HAIR AND SKIN OF THE HEAD OF A HUMAN BEINE WHICH COMPRISESTOPICALLY THERETO AN EFFECTIVE AMOUNT OF A COMPOUND OF THE FORMULA 2.The method according to claim 1, in which a hair shampoo, a hair rinseor a hairgrooming aid containing from about 0.001 to about 2.0 percentby weight of said compound is applied.